Autumn 2025 digital leaders retrospective

We held a retrospective with digital, content and communications leaders from a range of charities and not-for-profit organisations to gauge how things are going and share advice on what people are struggling with.

Here’s their pulse check on the sector and how they are navigating some of the challenges that everyone is facing in their organisations.

Navigating organisational change

There’s a lot of change going on in the sector right now: restructures, redundancies, team changes and instability, organisational strategy shifts and new services and approaches being launched.

The digital leaders talked through the importance of the ‘post-restructure world’ and ensuring that people who are still in the organisation feel motivated and valued. This comes in all shapes and sizes, from skills development to lack of micro-managing, and ensuring that the senior leadership understands the roles and functions of the teams. Here is some of their advice.

Involve the team in a new strategy

Work in partnership with the operational teams and leadership to define new strategy direction for the team. This people-centred approach will build understanding of how everyone’s role fits into the organisational strategy and enable team members to have a voice in this too.

Keep having open conversations

These should not be restricted to HR meetings during consultancy time, we should be having honest conversations about roles and responsibilities all the time. Try to schedule separate monthly reviews to operational one-to-ones to ensure you’re talking about how people are feeling in their roles, as well as project tasks.

Project planning

Many projects will have been affected during restructure processes, whether stalling because of internal knowledge gaps or hitting blockers because of time constraints. We reflected on the importance of building empathy – and therefore time – into the project planning process when organisational change and restructure is happening concurrently.

Digital trustee accelerating leadership digital skills development

Introducing a digital trustee to the board has been “game-changing” for one organisation as they now have specialist specific expertise at board level instead of broad marketing experience. Upskilling the other trustees has also been an added benefit of introducing the new digital trustee, enabling the whole board to increase their digital knowledge and acumen.

“We used to spend a lot of time and energy on trustees but it wasn’t driving projects forward. Now, the digital trustee pushes the other trustees on their lack of understanding of digital and technology. This not only educates the board, but also helps educate our executive leadership team too.”

This year’s Charity Digital Skills Report highlights that there’s work to be done in the sector to bring in more digital leadership, with 28% of charities saying that their boards have poor digital skills (a 9% increase since 2024) and only 30% of charities have a trustee with digital experience.

We’ll be revisiting this topic in future events as it resonates with so many organisations, particularly as we move into business planning and prioritisation conversations.

Have a firebreak

Being stuck in the day-to-day is a common theme in not progressing with strategy projects or shaping ways of working. One digital leader shared a recent ‘firebreak’ day they held to regroup on their content strategy.

Key components of their firebreak are to:

• allocate the time that you can, even if it’s only a day - remember that you can always allocate more time another month, it’s more important to make space now

• choose a specific problem and focus the time on solutions and building understanding

• meet in person if you can

• use a digital whiteboard during the session and reflect on it afterwards

• try not to spend time on emails or working on other projects

Not only did it focus on the problem and deliver some actionable solutions, but it positively impacted morale too.

“We lift each other up and we get into a room and have these big ideas and conversations, and it genuinely energises us all”

Improving quality of conversations on AI

Everyone is talking about AI, but some of the conversations have become existential or cyclical instead of driving solutions or bringing people on a journey.

One leader reflected that enabling and supporting others to have conversations, instead of always leading the discussions, has meant everyone has shared and reflected on an equal level.

“I’ve focused my role on holding the space, not filling the space.”

1. Work on a position statement and not a policy or a strategy

This gets people thinking about bigger-picture principles and ideas, rather than jumping straight into governance and rules.

2. Create a timeline and roadmap (with generous goals)

Shape the timeline collaboratively to reassure that, even though there’s a long way to go, there are small steps that can be taken in the interim.

Another benefit of a shared timeline is starting conversations about sequencing and testing AI implementation iteratively as part of a plan and not on a whim.

Underpinning all of this should be a supportive approach, led with curiosity and a mindset of taking each step collectively, to better everyone’s understanding and engage with AI incrementally.

“It’s fine that we’re not there yet, but we will be.”

Content models: decentralised vs centralised

We reflected that, as a sector, we have become stuck on deciding between decentralisation or centralised content processes, and instead we need to look at a more nuanced way of looking at content processes, governance and production.

One organisation has successfully started these conversations by:

• stepping back to consider what they want the content team to be and how they want to support other teams
• trying out new models including content strategy partnering
• categorising content creators with more attributes than purely the team they are in, including the volume of content they create, their content maturity and their skills

Thinking about the needs of their content creators across the organisation, alongside their website objectives, has helped them to see opportunities, skills and how to map roles and responsibilities for new content planning and governance processes.

Conclusion

This session was a reminder of how shared the challenges are, and how much we all benefit from hearing them out loud.

Thanks for joining us

Caitlin Pearce (Parkinson’s UK), Graeme Manuel-Jones (BookTrust), Katherine Newbigging (Locality), Matthew Farrand (Maudsley Charity), Florence Battersby-Bates (John Lyons Charity), Rumneek Haas (Change Grow Live), Alex Anning (Changing Faces UK), Kyra Swaby (King George & Queen’s Hospitals Charity), Stephanie Stanesby (Face Equality International), Frankie Wardzinski (Scope) and Stephanie Parker (Marie Curie).

Next retrospective

Our next digital leaders retro is on 15 January 2026, where we’ll be chatting about plans and priorities for the new year.

Sign up to secure your place – spaces are limited!